N⁶-benzoyl-9-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]adenine

Base Information

• Chemical Name: N⁶-benzoyl-9-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]adenine
• CAS No.: 457653-17-7
• Molecular Formula: C₃₁H₃₇N₅O₃SSeSi
• Molecular Weight: 666.778

Synonyms:N⁶-benzoyl-9-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]adenine

Chemical Property of N⁶-benzoyl-9-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]adenine

Chemical Property:

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Technology Process of N⁶-benzoyl-9-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]adenine

There total 12 articles about N⁶-benzoyl-9-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]adenine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 51.0%

Phenylselenyl chloride (5707-04-0) + 6-benzoylamino-9-trimethylsilylpurine (60855-35-8) + 1,4-anhydro-2-deoxy-3,5-O-(di-tert-butylsilylene)-4-thio-D-erythro-pento-1-enitol (209048-62-4) → N6-benzoyl-1-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]adenine (457653-22-4) + N6-benzoyl-7-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]adenine (457653-20-2) + N6-benzoyl-9-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]adenine (457653-17-7)

Guidance literature:

In acetonitrile; at 0 ℃;

DOI:10.1021/jo020037x

Reference yield: 30.0%

Phenylselenyl chloride (5707-04-0) + bis(trimethylsilyl)-N6-benzoyladenine (18055-46-4) + 1,4-anhydro-2-deoxy-3,5-O-(di-tert-butylsilylene)-4-thio-D-erythro-pento-1-enitol (209048-62-4) → N6-benzoyl-1-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]adenine (457653-22-4) + N6-benzoyl-7-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]adenine (457653-20-2) + N6-benzoyl-9-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]adenine (457653-17-7)

Guidance literature:

In acetonitrile; at 0 ℃;

DOI:10.1021/jo020037x

Reference yield:

(2R,3S)-5-(benzylthio)-2-(hydroxymethyl)tetrahydrothiophen-3-ol (134700-25-7) → N6-benzoyl-9-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]adenine (457653-17-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 5.46 g / imidazole; DMF / 20 °C

2: acetic acid / 2 h / 20 °C

3: 670 mg / ammonia / methanol / 20 °C

4: 4-dimethylaminopyridine / CH₂Cl₂ / 0 °C

5: 113 mg / CH₂Cl₂ / 20 °C

6: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

7: 30.9 mg / 4-(dimethylamino)pyridine; DMF / 0 °C

8: 6 percent / acetonitrile / 0 °C

With 1H-imidazole; dmap; tetrabutyl ammonium fluoride; ammonia; acetic acid; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1021/jo020037x

upstream raw materials:

Phenylselenyl chloride

bis(trimethylsilyl)-N⁶-benzoyladenine

1,4-anhydro-2-deoxy-3,5-O-(di-tert-butylsilylene)-4-thio-D-erythro-pento-1-enitol

6-benzoylamino-9-trimethylsilylpurine

Downstream raw materials:

N⁶-benzoyl-9-[3,5-O-(di-tert-butylsilylene)-2-deoxy-4-thio-β-D-ribofuranosyl]adenine

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